Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone

In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through a radical difunctionalization of alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis and an open-flask atmosphere, and the reaction is highlighted with good yields and a broad reaction scope. Mechanism studies show that the reaction is initiated by a formal [4 + 2] cyclization of the sulfonyl radical in a regioselective manner.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-26
DOI
https://doi.org/10.1021/acs.joc.4c02720
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.50

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article

Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone

Guanyinsheng Qiu, N. F. Chen, Xingxian Zhang, Yiliang Liao et al.
2 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
0.50
article

Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone

Guanyinsheng Qiu, N. F. Chen, Xingxian Zhang, Yiliang Liao, Meng Guan, Chen Bao, Xinyu Zhu
article en
2 citations

Abstract

In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through a radical difunctionalization of alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis and an open-flask atmosphere, and the reaction is highlighted with good yields and a broad reaction scope. Mechanism studies show that the reaction is initiated by a formal [4 + 2] cyclization of the sulfonyl radical in a regioselective manner.

The Journal of Organic ChemistryVol. 90(1)
Jiaxing University (CN), Jiaxing Vocational Technical College (CN), Pharmaceutical Biotechnology (Czechia) (CZ), Zhejiang University of Technology (CN)
National Natural Science Foundation of China
Zero hunger
Openalex Percentile: Top 37%
Sulfur-Based Synthesis Techniques
0.50
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